N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide → N-(2-fluoro-5-aminophenyl)-3,4,5,6-tetrahydrophthalimide

Participants

Reaction Steps

To a suspension of electrolytic iron powders (9 g) in 5% acetic acid (200 g) under reflux, a solution of N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide (VII) (15 g) in acetic acid (50 g) was added dropwise. After completion of the addition, the resultant mixture was heated under reflux for 30 minutes, cooled and filtered. The filtrate was diluted with water and extracted with ethyl acetate. The extract was concentrated, and the precipitated crystals were collected by filtration to give 10.5 g of N-(2-fluoro-5-aminophenyl)-3,4,5,6-tetrahydrophthalimide (VIII). M.P., 117°-119° C.

Provenance & Evidence